Hydrochloric Acid → HCID 178505168, compound

HRID 2083943Notes

Reaction equation

HRID 2083943 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:19])[NH2:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:25][S:26](Cl)(=[O:28])=[O:27].Cl>CC(C)=O.O.CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[NH:18])[NH:19][S:26]([CH3:25])(=[O:28])=[O:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178512917HCID 178512917, compound

Product 1

HCID 178505168HCID 178505168, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To 10 mmol of (S)-N2-(benzyloxycarbonyl)-arginine suspended in a mixture of acetone/water 80/20 there is added, at 0° C., a sufficient amount of 4N sodium hydroxide solution to bring the pH of the reaction mixture to between 11 and 11.5. After stirring for 2 hours, there is then added a solution of methanesulphonyl chloride in acetone and then, after stirring for a further 3 hours, the mixture is neutralised using 1N hydrochloric acid solution; the acetone is then evaporated off, and the residue obtained is extracted with ether and then washed, dried, filtered and evaporated. The pale yellow oil thereby obtained is purified by chromatography over silica (eluant: dichloromethane/methanol 7/3) to yield the expected product in the form of a whitish meringue.

Workup

  1. additionis added, at 0° C.
  2. stirringafter stirring for a further 3 hours
  3. customthe acetone is then evaporated off
  4. customthe residue obtained
  5. extractionis extracted with ether
  6. washwashed
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe pale yellow oil thereby obtained
  11. customis purified by chromatography over silica (eluant: dichloromethane/methanol 7/3)

Sources & evidence

ORD record
ord-9e6e93c9e5274921bc88c27910dd2d31
Source dataset
uspto-grants-2004_04
Patent number
US06716843B2

Reaction notes

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